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A Quantum-Chemical Study of Tautomeric Equilibria of Fluorescein Dyes in DMSO

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Chemistry of Heterocyclic Compounds Aims and scope

We evaluated the relative thermodynamic stability of various molecular and anionic tautomers of fluorescein, its 2,4,5,7-tetrabromo derivative (eosin), and also sulfofluorescein, 4'- and 5'-amino-fluoresceins, and 2,4,5,7-tetranitrofluorescein in DMSO, based on a quantum-chemical investigation; in some cases the calculations were performed for gas phase and aqueous solutions. These results, obtained for 39 structures (15 of which were studied by quantum-chemical methods for the first time) generally agree with the previously published experimental data.

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Authors and Affiliations

  1. V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61022, Ukraine

    A. V. Lebed, A. V. Biryukov & N. O. Mchedlov-Petrossyan

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  1. A. V. Lebed
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  2. A. V. Biryukov
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  3. N. O. Mchedlov-Petrossyan
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Correspondence to A. V. Lebed.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 367-380, 2014.

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Lebed, A.V., Biryukov, A.V. & Mchedlov-Petrossyan, N.O. A Quantum-Chemical Study of Tautomeric Equilibria of Fluorescein Dyes in DMSO. Chem Heterocycl Comp 50, 336–348 (2014). https://doi.org/10.1007/s10593-014-1481-8

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